(4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one → (R)-4-(2-(1-Ethyl-1H-pyrrol-2-yl)ethyl)-4-methyloxazolidin-2-one

HRID 604561Notes

Reaction equation

HRID 604561 reaction equation
[CH3:1][C@@:2]1([CH:8]=[CH:9][C:10]2[N:11]([CH2:15][CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1>C(O)C.[C].[Pd]>[CH3:1][C@@:2]1([CH2:8][CH2:9][C:10]2[N:11]([CH2:15][CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1

Participants

4

Reactant 1

HCID 66673008(4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one

Product 1

HCID 45095485(R)-4-(2-(1-Ethyl-1H-pyrrol-2-yl)ethyl)-4-methyloxazolidin-2-oneYield 87%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×

Procedure

10% Palladium-carbon (500 mg, 50% hydrous) was suspended in ethanol (10 mL) and a solution of (4R)-4-methyl-4-[2-(1-ethylpyrrol-2-yl)ethenyl]-1,3-oxazolidin-2-one (5.7 g, 25.9 mmol) obtained in Reference example 3 (3c) in ethanol (50 mL) was added thereto, followed by stirring of the mixture at room temperature under a hydrogen atmosphere for 1 hour. After the palladium-carbon in the reaction mixture was Celite-filtered, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane: ethyl acetate, 3:7) to obtain the title compound (5.0 g, yield: 87%).

Workup

  1. additionwas added
  2. filtrationAfter the palladium-carbon in the reaction mixture was Celite-filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane: ethyl acetate, 3:7)

Sources & evidence

ORD record
ord-16c769819c394f69a29465addf42adf7
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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